Exchange 2013 - Outlook connection problem

[burgemaster]

Hi all,

 

Im hoping this is really easy!!!!!!

 

email server: email.XXXXX.worcs.sch.uk

external address: webmail.XXXXX.worcs.sch.uk

internal self signed SSL: email.XXXXX.local

external SSL: webmail.XXXXX.worcs.sch.uk

 

We have upgraded from 2007 > 2013 exchange. We have migrated a couple of test mailboxes over and I am having trouble with the certificates.

When I try and connect outlook on domain joined machines, I get an SSL warning that the name on the cert is incorrect..

 

The problem appears to be that outlook is trying to connect to our external address: webmail.XXXXXX.worcs.sch.uk

Can anyone please advice how we change how outlook connects?

Im guessing outlook should be connecting to "email.XXXXX.local" when on domain joined PCs?

 

Thanks in advance!!!!

[NikChillin]

We just updated our certificates with Godaddy and are now getting signature verification errors.

 

ours is with the xxxx.school part, we can't have that anymore because of the new domain names apparently, maybe the same for you with the xxxx.local extension?

 

Are you using a 'SAN' cert?

Edited July 31, 2014 by NikChillin

[Demarcation]

in the exchange server set both the internal and external addresses to use the external web addresses and set yoru certificate up with that.

[burgemaster]

We used split DNS and as suggested above setup everything with the external address.

[harriuk]

Yes we have also done the same as the above two posts.